Best events in
Cragsmoor

The Shawangunk Ridge offers a quiet weekday rhythm, but weekends bring a variety of events and things to do in Cragsmoor, NY and its neighboring towns. The local culture often pairs daytime outdoor exploration in places like Sam's Point Preserve with an evening of professional theater or live music. This legacy as an artists' colony remains present, with galleries, summer concert series, and annual studio tours dotting the landscape.

A classic evening out often involves dinner in downtown Ellenville before catching a professional performance at the historic Shadowland Stages.
Live music venues like The Falcon in Marlboro and The Colony in Woodstock host a regular rotation of regional and touring acts.
The region's creative spirit is on full display during annual events like the Upstate Art Weekend and the Borscht Belt Fest.

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Events near Cragsmoor

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AI & Education: A Community Conversation

Tomorrow • 6:30 PM

North River Electric House

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Flash Foxy - Trad Mentorship - New Paltz, NY

Saturday • 8:00 AM

Peterskill At Minnewaska State Park Preserve

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Nov 7 Sat: Hike Gertrude's Nose and Millbrook Mtn Loop w Transport $55

Saturday • 6:30 AM

Gertrude's Nose Trailhead

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Nov 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

Thu, Nov 12 • 8:00 AM

Town of Wallkill Golf Club

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2026 Computer Science Teachers Association New York Conference

Sat, Nov 14 • 8:00 AM

State University of New York at New Paltz

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SUNY Sullivan 2026 Holiday Craft Fair - Vendor Application

Sat, Nov 21 • 11:00 AM

SUNY Sullivan

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Mystic Sound Journey

Sat, Nov 21 • 7:00 PM

The Sound Womb

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2026 Lunch of Honor

Sun, Dec 6 • 1:00 PM

Resorts World Catskills

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AI & Education: A Community Conversation

Tomorrow • 6:30 PM

North River Electric House

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Flash Foxy - Trad Mentorship - New Paltz, NY

Saturday • 8:00 AM

Peterskill At Minnewaska State Park Preserve

Check ticket price on event

Nov 7 Sat: Hike Gertrude's Nose and Millbrook Mtn Loop w Transport $55

Saturday • 6:30 AM

Gertrude's Nose Trailhead

Check ticket price on event

Nov 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

Thu, Nov 12 • 8:00 AM

Town of Wallkill Golf Club

Check ticket price on event

2026 Computer Science Teachers Association New York Conference

Sat, Nov 14 • 8:00 AM

State University of New York at New Paltz

Check ticket price on event

SUNY Sullivan 2026 Holiday Craft Fair - Vendor Application

Sat, Nov 21 • 11:00 AM

SUNY Sullivan

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Mystic Sound Journey

Sat, Nov 21 • 7:00 PM

The Sound Womb

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2026 Lunch of Honor

Sun, Dec 6 • 1:00 PM

Resorts World Catskills

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Port Jervis

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Ringwood

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Danbury

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Rhinebeck

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Peekskill

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Wanaque

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Ossining

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Lake Mohawk

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New Paltz

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Scotchtown

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Stony Point

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Saugerties

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Highland

22 miles away

Rosendale Hamlet

20 miles away

Online Events

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

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This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

Check ticket price on event

This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

Check ticket price on event

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

Check ticket price on event

How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Points of Interest near Cragsmoor

Bear Hill Nature Preserve

Frequently asked questions about Cragsmoor

Where are the best spots for live music events near Cragsmoor?

The Falcon in Marlboro is a premier destination for live music, often with no cover charge. It hosts acclaimed musicians on its main stage and smaller sessions in The Falcon Underground. The Colony in Woodstock is another key venue with an indoor stage and outdoor beer garden.

What are some date night ideas in the Cragsmoor area?

A popular date night involves dinner in Ellenville followed by a show at Shadowland Stages. The professional theater presents a year-round season of plays and musicals in a historic building. For a more casual evening, consider finding live music at a venue with an outdoor space.

Are there notable art events or festivals near Cragsmoor?

The annual Upstate Art Weekend is a major highlight for art lovers in the region. During this multi-day summer event, galleries, artist studios, and cultural centers open their doors for special exhibitions. The historic Cragsmoor Stone Church also hosts cultural events and summer concerts.

How can I find free events around Cragsmoor?

The Falcon in Marlboro frequently offers world-class music events with no cover, encouraging donations instead. Additionally, Pine Bush First Fridays is a free-to-attend street fair running from May through December, featuring live music, artisans, and food vendors on Main Street.

What are some family-friendly events in the area?

The annual Ellenville Blueberry Festival is a popular family-friendly street fair each summer. It offers live music, food, and activities celebrating the local harvest. The seasonal Ellenville and Kingston Farmers Markets are also great for a family outing.

Can I find comedy shows near Cragsmoor?

The Colony in Woodstock is a reliable venue for finding stand-up comedy in its lineup of performances. The venue also hosts a weekly open mic night, which can feature a mix of music and comedy from local and emerging talent.

What kind of outdoor events happen near Cragsmoor?

Sam's Point Preserve offers more than just its famous Ice Caves and hiking trails. The preserve hosts various public programs and guided nature walks, providing structured outdoor events that explore the Shawangunk Ridge's unique ecology and landscape.

What community events celebrate the local culture?

The Borscht Belt Fest is an annual Ellenville event celebrating the region's historic culture. It features live music, performances, and food vendors. For a recurring local gathering, Pine Bush First Fridays brings the community together on Main Street with music and artisans.

Events near Cragsmoor

AI & Education: A Community Conversation

Flash Foxy - Trad Mentorship - New Paltz, NY

Nov 7 Sat: Hike Gertrude's Nose and Millbrook Mtn Loop w Transport $55

Nov 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

2026 Computer Science Teachers Association New York Conference

SUNY Sullivan 2026 Holiday Craft Fair - Vendor Application

Mystic Sound Journey

2026 Lunch of Honor

AI & Education: A Community Conversation

Flash Foxy - Trad Mentorship - New Paltz, NY

Nov 7 Sat: Hike Gertrude's Nose and Millbrook Mtn Loop w Transport $55

Nov 2026 Seminar for Water and Wastewater Operators, PEs, and Non-Members

2026 Computer Science Teachers Association New York Conference

SUNY Sullivan 2026 Holiday Craft Fair - Vendor Application

Mystic Sound Journey

2026 Lunch of Honor

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Nearby cities

Kingston

Pompton Lakes

Woodstock

Beacon

Poughkeepsie

Carmel Hamlet

Newburgh

Merritt Park

Mount Ivy

Mount Pleasant

Nyack

North Haledon

Blauvelt

Mount Kisco

Port Jervis

Ringwood

Tarrytown

Danbury

Rhinebeck

Ridgewood

Peekskill

Wanaque

Ossining

Lake Mohawk

New Paltz

Scotchtown

Stony Point

Saugerties

Highland

Rosendale Hamlet

Kingston

Pompton Lakes

Woodstock

Beacon

Poughkeepsie

Carmel Hamlet

Newburgh

Merritt Park

Mount Ivy

Mount Pleasant

Nyack

North Haledon

Blauvelt

Mount Kisco

Port Jervis

Ringwood

Tarrytown

Danbury

Rhinebeck

Ridgewood

Peekskill

Wanaque

Ossining

Lake Mohawk

New Paltz

Scotchtown